I am trying to get email out of AWS image to google on port 587. When I use telnet it connects - so 587 is a valid path... telnet smtp-relay.gmail.com 587 Trying 142.250.112.28... Connected to smtp-relay.gmail.com. Escape character is '^]'. 220 smtp-relay.gmail.com ESMTP l15-20020a17090a150f00b001dfac278995sm682651pja.12 - gsmtp ^]quit When I run interactive session: sendmail -Am -v -t To: X at Y From: X at Y Subject: test X at Y... Connecting to aspmx.l.google.com. port 587 via esmtp... sendmail.mc has define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl define(`RELAY_MAILER', `esmtp')dnl define(`null_client', `smtp-relay.gmail.com.') I dont understand why 587 is not connecting. It connects on the manual telnet. It does not connect otherwise. What might I be missing? Jerry